Dicarboxylic acid

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Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkyl, alkenyl, or akynyl group. Dicarboxylic acids can be used to prepare copolymers such as nylon and polyethylene terephthalate.

In general, dicarboxylic acids show the same chemical behaviour and reactivity as monocarboxylic acids. The ionization of the second carboxyl group occurs less readily than the first one. This is because more energy is required to separate a positive hydrogen ion from the doubly charged anion than from the single charged anion.

A mnemonic to aid in remembering the order of the common nomenclature for the first six dicarboxylic acids is "Oh my, such great apple pie!" (oxalic, malonic, succinic, glutaric, adipic, pimelic).

When one of the carboxy groups is replaced with an aldehyde group, the resulting structure is called a "aldehydic acid".


Elementary dicarboxylic acids
Common name IUPAC name Chemical formula Structural formula
Oxalic acid ethanedioic acid HOOC-COOH Oxalic acid.png
Malonic acid propanedioic acid HOOC-(CH2)-COOH 90px
Succinic acid butanedioic acid HOOC-(CH2)2-COOH 100px
Glutaric acid pentanedioic acid HOOC-(CH2)3-COOH 100px
Adipic acid hexanedioic acid HOOC-(CH2)4-COOH 150px
Pimelic acid heptanedioic acid HOOC-(CH2)5-COOH 170px
Suberic acid octanedioic acid HOOC-(CH2)6-COOH 200px
Azelaic acid nonanedioic acid HOOC-(CH2)7-COOH Azelaic acid.svg
Sebacic acid decanedioic acid HOOC-(CH2)8-COOH 240px
Phthalic acid benzene-1,2-dicarboxylic acid
o-phthalic acid
C6H4(COOH)2 125px
Isophthalic acid benzene-1,3-dicarboxylic acid
m-phthalic acid
C6H4(COOH)2 125px
Terephthalic acid benzene-1,4-dicarboxylic acid
p-phthalic acid
C6H4(COOH)2 125px

See Category:Dicarboxylic acids for a list.

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